JPS6256880B2 - - Google Patents
Info
- Publication number
- JPS6256880B2 JPS6256880B2 JP54137534A JP13753479A JPS6256880B2 JP S6256880 B2 JPS6256880 B2 JP S6256880B2 JP 54137534 A JP54137534 A JP 54137534A JP 13753479 A JP13753479 A JP 13753479A JP S6256880 B2 JPS6256880 B2 JP S6256880B2
- Authority
- JP
- Japan
- Prior art keywords
- mol
- hydrogen
- mixture
- solution
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 19
- 229960002429 proline Drugs 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- -1 alkali metal salts Chemical class 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 238000004809 thin layer chromatography Methods 0.000 description 15
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 238000010992 reflux Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000005909 Kieselgur Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000012154 double-distilled water Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- IWCGEJKKDAJKJE-UHFFFAOYSA-N n-(benzyldiazenyl)-4-methylaniline Chemical compound C1=CC(C)=CC=C1NN=NCC1=CC=CC=C1 IWCGEJKKDAJKJE-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 206010020772 Hypertension Diseases 0.000 description 4
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000001962 electrophoresis Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 4
- RTSMKJMWBXDORQ-UHFFFAOYSA-N 2-[methyl(phenylmethoxy)phosphoryl]acetic acid Chemical compound OC(=O)CP(=O)(C)OCC1=CC=CC=C1 RTSMKJMWBXDORQ-UHFFFAOYSA-N 0.000 description 3
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 3
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- 229930182821 L-proline Natural products 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 239000003929 acidic solution Substances 0.000 description 3
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 3
- 239000001099 ammonium carbonate Substances 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- HGGAGFSIROMXCT-UHFFFAOYSA-N dimethylphosphoryloxymethylbenzene Chemical compound CP(C)(=O)OCC1=CC=CC=C1 HGGAGFSIROMXCT-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000013930 proline Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- IHJCJVSDTXBLBL-UHFFFAOYSA-N 2-[hydroxy(2-phenylethyl)phosphoryl]acetic acid Chemical compound OC(=O)CP(O)(=O)CCC1=CC=CC=C1 IHJCJVSDTXBLBL-UHFFFAOYSA-N 0.000 description 2
- ZPUMRJBPULBAPN-UHFFFAOYSA-N 2-[hydroxy(3-phenylpropyl)phosphoryl]acetic acid Chemical compound OC(=O)CP(O)(=O)CCCC1=CC=CC=C1 ZPUMRJBPULBAPN-UHFFFAOYSA-N 0.000 description 2
- RXJYXHJDPUQFFI-UHFFFAOYSA-N 2-[phenyl(phenylmethoxy)phosphoryl]acetic acid Chemical compound C=1C=CC=CC=1P(=O)(CC(=O)O)OCC1=CC=CC=C1 RXJYXHJDPUQFFI-UHFFFAOYSA-N 0.000 description 2
- 239000005541 ACE inhibitor Substances 0.000 description 2
- 102000015427 Angiotensins Human genes 0.000 description 2
- 108010064733 Angiotensins Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PUKKNDJROZWPKK-UHFFFAOYSA-N OCP(=O)CC(O)=O Chemical compound OCP(=O)CC(O)=O PUKKNDJROZWPKK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- CVNMBKFJYRAHPO-UHFFFAOYSA-N [chloro(methyl)phosphoryl]methane Chemical compound CP(C)(Cl)=O CVNMBKFJYRAHPO-UHFFFAOYSA-N 0.000 description 2
- 238000004847 absorption spectroscopy Methods 0.000 description 2
- 150000007513 acids Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- VVCLBQFBKZQOAF-NSHDSACASA-N benzyl (2s)-pyrrolidine-2-carboxylate Chemical compound O=C([C@H]1NCCC1)OCC1=CC=CC=C1 VVCLBQFBKZQOAF-NSHDSACASA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- GOJNABIZVJCYFL-UHFFFAOYSA-N dimethylphosphinic acid Chemical compound CP(C)(O)=O GOJNABIZVJCYFL-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- BBZGFGDJIKLOMN-UHFFFAOYSA-N methyl 2-[methyl(phenylmethoxy)phosphoryl]acetate Chemical compound COC(=O)CP(C)(=O)OCC1=CC=CC=C1 BBZGFGDJIKLOMN-UHFFFAOYSA-N 0.000 description 2
- RMJCJLHZCBFPDN-UHFFFAOYSA-N methyl(phenyl)phosphinic acid Chemical compound CP(O)(=O)C1=CC=CC=C1 RMJCJLHZCBFPDN-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010647 peptide synthesis reaction Methods 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 150000003148 prolines Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WZQIUYFHTJZDLH-UHFFFAOYSA-N (2-methoxy-2-oxoethyl)-(3-phenylpropyl)phosphinic acid Chemical compound COC(CP(=O)(CCCC1=CC=CC=C1)O)=O WZQIUYFHTJZDLH-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- YEOUKYLGAGZSGK-UHFFFAOYSA-N 2-[2-phenylethyl(phenylmethoxy)phosphoryl]acetic acid Chemical compound C=1C=CC=CC=1COP(=O)(CC(=O)O)CCC1=CC=CC=C1 YEOUKYLGAGZSGK-UHFFFAOYSA-N 0.000 description 1
- YWQOUILYEIYAMN-UHFFFAOYSA-N 2-[methyl(phenyl)phosphoryl]oxyethylbenzene Chemical compound C=1C=CC=CC=1P(=O)(C)OCCC1=CC=CC=C1 YWQOUILYEIYAMN-UHFFFAOYSA-N 0.000 description 1
- PVRHPTDMJVSVQT-UHFFFAOYSA-N 2-[phenylmethoxy(3-phenylpropyl)phosphoryl]acetic acid Chemical compound C=1C=CC=CC=1COP(=O)(CC(=O)O)CCCC1=CC=CC=C1 PVRHPTDMJVSVQT-UHFFFAOYSA-N 0.000 description 1
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- GPRQVQIDIJJIHD-UHFFFAOYSA-N 2-phenylethylphosphinic acid Chemical compound OP(=O)CCC1=CC=CC=C1 GPRQVQIDIJJIHD-UHFFFAOYSA-N 0.000 description 1
- CUGDFDWMNKYVMV-UHFFFAOYSA-N 2-phosphorosoacetic acid Chemical compound OC(=O)CP=O CUGDFDWMNKYVMV-UHFFFAOYSA-N 0.000 description 1
- XMZQWZJMTBCUFT-UHFFFAOYSA-N 3-bromopropylbenzene Chemical compound BrCCCC1=CC=CC=C1 XMZQWZJMTBCUFT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 description 1
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- AQZDUDDYRCYLHK-UHFFFAOYSA-N CC(C(O)=O)(OCC1=CC=CC=C1)[PH2]=O Chemical compound CC(C(O)=O)(OCC1=CC=CC=C1)[PH2]=O AQZDUDDYRCYLHK-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 238000000023 Kugelrohr distillation Methods 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
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- WWDMDHUOYPEXQH-UHFFFAOYSA-N chloro(phenoxy)phosphinic acid Chemical compound OP(Cl)(=O)OC1=CC=CC=C1 WWDMDHUOYPEXQH-UHFFFAOYSA-N 0.000 description 1
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- MLCHBQKMVKNBOV-UHFFFAOYSA-M dioxido(phenyl)phosphanium Chemical compound [O-]P(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-M 0.000 description 1
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- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657172—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C07F9/304—Aromatic acids (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C07F9/306—Arylalkanephosphinic acids, e.g. Ar-(CH2)n-P(=X)(R)(XH), (X = O,S, Se; n>=1)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3229—Esters of aromatic acids (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3241—Esters of arylalkanephosphinic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3288—Esters with arylalkanols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/34—Halides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/4816—Acyclic saturated acids or derivatices which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4891—Monohalide derivatives RP (XR') (Hal) (X = O, S, N)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/953,711 US4168267A (en) | 1978-10-23 | 1978-10-23 | Phosphinylalkanoyl prolines |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5557597A JPS5557597A (en) | 1980-04-28 |
JPS6256880B2 true JPS6256880B2 (US07202987-20070410-C00007.png) | 1987-11-27 |
Family
ID=25494430
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP13753479A Granted JPS5557597A (en) | 1978-10-23 | 1979-10-23 | Phosfinylalkanoylprolines and their manufacture |
Country Status (18)
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6435273U (US07202987-20070410-C00007.png) * | 1987-08-26 | 1989-03-03 |
Families Citing this family (118)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6458772B1 (en) | 1909-10-07 | 2002-10-01 | Medivir Ab | Prodrugs |
US4690940A (en) * | 1979-08-14 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
US4690939A (en) * | 1979-08-14 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
US4698355A (en) * | 1979-08-14 | 1987-10-06 | University Of Miami | Anti-hypertensive agents |
US4695577A (en) * | 1979-08-14 | 1987-09-22 | University Of Miami | Anti-hypertensive agents |
ZA794723B (en) * | 1978-09-11 | 1980-08-27 | Univ Miami | Anti-hypertensive agents |
US4698356A (en) * | 1979-08-14 | 1987-10-06 | University Of Miami | Anti-hypertensive agents |
US4690938A (en) * | 1979-08-14 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
US4690937A (en) * | 1979-08-14 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
US4168267A (en) * | 1978-10-23 | 1979-09-18 | E. R. Squibb & Sons, Inc. | Phosphinylalkanoyl prolines |
US4690936A (en) * | 1980-03-05 | 1987-09-01 | University Of Miami | Anti-hypertensive agents |
US4734420A (en) * | 1980-03-05 | 1988-03-29 | University Of Miami | Anti-hypertensive agents |
US4312809A (en) * | 1980-10-31 | 1982-01-26 | E. R. Squibb & Sons, Inc. | Lactam derivatives of mercaptoacylamino acids |
US4384123A (en) * | 1980-12-04 | 1983-05-17 | E. R. Squibb & Sons, Inc. | Phosphinylalkanoyl substituted prolines |
US4337201A (en) * | 1980-12-04 | 1982-06-29 | E. R. Squibb & Sons, Inc. | Phosphinylalkanoyl substituted prolines |
US4379146A (en) * | 1981-02-17 | 1983-04-05 | Merck & Co., Inc. | Substituted phosphonamides as antihypertensives |
US4374131A (en) * | 1981-04-27 | 1983-02-15 | E. R. Squibb & Sons, Inc. | Amino and substituted amino phosphinyl-alkanoyl compounds |
US4416831A (en) * | 1981-04-27 | 1983-11-22 | E. R. Squibb & Sons, Inc. | Amino and substituted amino phosphinylalkanoyl compounds |
US4416833A (en) * | 1981-05-04 | 1983-11-22 | E. R. Squibb & Sons, Inc. | Substituted carbonyl phosphinyl-alkanoyl compounds |
US4381297A (en) * | 1981-05-04 | 1983-04-26 | E. R. Squibb & Sons, Inc. | Substituted carbonyl phosphinyl-alkanoyl compounds |
EP0070131A1 (en) * | 1981-07-09 | 1983-01-19 | Analytical Research Pharmaceuticals Pty. Ltd. | Phosphonoalkanoylamino acids |
US4432971A (en) * | 1981-08-03 | 1984-02-21 | E. R. Squibb & Sons, Inc. | Phosphonamidate compounds |
US4432972A (en) * | 1981-08-03 | 1984-02-21 | E. R. Squibb & Sons, Inc. | Phosphonamidate compounds |
US4371526A (en) * | 1981-08-21 | 1983-02-01 | E. R. Squibb & Sons, Inc. | Phosphinylalkanoyl substituted 4,5-dihydropyrazole-5-carboxylic acid derivatives and hypotensive method and composition |
EP0075334A3 (en) * | 1981-09-25 | 1984-03-21 | The Wellcome Foundation Limited | Pharmaceutical compounds, and preparation, formulations and use thereof |
US4396772A (en) * | 1981-11-23 | 1983-08-02 | F. R. Squibb & Sons, Inc. | Phosphinylalkanoyl amino acids |
US4555506A (en) * | 1981-12-24 | 1985-11-26 | E. R. Squibb & Sons, Inc. | Phosphorus containing compounds and use as hypotensives |
US4716155A (en) * | 1981-12-24 | 1987-12-29 | E. R. Squibb & Sons, Inc. | Phosphorus containing compounds and hypotensive use thereof |
US4452791A (en) * | 1982-03-15 | 1984-06-05 | E. R. Squibb & Sons, Inc. | Aminoalkyl and related substituted phosphinic acid angiotensin converting enzyme inhibitors |
US4560680A (en) * | 1982-03-15 | 1985-12-24 | E. R. Squibb & Sons, Inc. | Aminoalkyl and related substituted phosphinic acid angiotensin converting enzyme inhibitors |
EP0091525A3 (en) * | 1982-04-08 | 1984-02-29 | Analytical Research Pharmaceuticals Pty. Ltd. | Phosphonoalkanoylamino acids |
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FR2288100A1 (fr) * | 1974-10-17 | 1976-05-14 | Poudres & Explosifs Ste Nale | Carbamates phosphonates, leur procede de preparation et leurs applications en tant qu'agents d'ignifugation |
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US4151172A (en) * | 1977-08-11 | 1979-04-24 | E. R. Squibb & Sons, Inc. | Phosphonoacyl prolines and related compounds |
US4168267A (en) * | 1978-10-23 | 1979-09-18 | E. R. Squibb & Sons, Inc. | Phosphinylalkanoyl prolines |
-
1978
- 1978-10-23 US US05/953,711 patent/US4168267A/en not_active Expired - Lifetime
-
1979
- 1979-09-20 CA CA335,993A patent/CA1133496A/en not_active Expired
- 1979-09-24 ZA ZA00795048A patent/ZA795048B/xx unknown
- 1979-09-27 GB GB7933627A patent/GB2031897B/en not_active Expired
- 1979-09-28 AU AU51300/79A patent/AU529134B2/en not_active Ceased
- 1979-10-05 IE IE1895/79A patent/IE49020B1/en not_active IP Right Cessation
- 1979-10-05 PH PH23126A patent/PH13931A/en unknown
- 1979-10-09 FR FR7925088A patent/FR2439790A1/fr active Granted
- 1979-10-12 NL NL7907568A patent/NL7907568A/nl not_active Application Discontinuation
- 1979-10-22 SU SU792835388A patent/SU988194A3/ru active
- 1979-10-22 CH CH945979A patent/CH645382A5/de not_active IP Right Cessation
- 1979-10-22 IT IT26704/79A patent/IT1125558B/it active
- 1979-10-22 LU LU81809A patent/LU81809A1/fr unknown
- 1979-10-22 DK DK445579A patent/DK148141C/da not_active IP Right Cessation
- 1979-10-22 SE SE7908727A patent/SE7908727L/xx not_active Application Discontinuation
- 1979-10-23 DE DE19792942781 patent/DE2942781A1/de not_active Ceased
- 1979-10-23 BE BE0/197783A patent/BE879586A/fr not_active IP Right Cessation
- 1979-10-23 JP JP13753479A patent/JPS5557597A/ja active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6435273U (US07202987-20070410-C00007.png) * | 1987-08-26 | 1989-03-03 |
Also Published As
Publication number | Publication date |
---|---|
CH645382A5 (de) | 1984-09-28 |
DK445579A (da) | 1980-04-24 |
FR2439790B1 (US07202987-20070410-C00007.png) | 1984-01-13 |
ZA795048B (en) | 1980-09-24 |
IT1125558B (it) | 1986-05-14 |
JPS5557597A (en) | 1980-04-28 |
US4168267A (en) | 1979-09-18 |
CA1133496A (en) | 1982-10-12 |
IE49020B1 (en) | 1985-07-10 |
BE879586A (fr) | 1980-04-23 |
GB2031897B (en) | 1983-03-02 |
GB2031897A (en) | 1980-04-30 |
AU5130079A (en) | 1980-05-01 |
DK148141C (da) | 1985-09-02 |
LU81809A1 (fr) | 1980-01-25 |
NL7907568A (nl) | 1980-04-25 |
IE791895L (en) | 1980-04-23 |
DE2942781A1 (de) | 1980-04-30 |
FR2439790A1 (fr) | 1980-05-23 |
SU988194A3 (ru) | 1983-01-07 |
SE7908727L (sv) | 1980-06-12 |
DK148141B (da) | 1985-03-18 |
PH13931A (en) | 1980-11-04 |
AU529134B2 (en) | 1983-05-26 |
IT7926704A0 (it) | 1979-10-22 |
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